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Volumn 36, Issue 11, 1997, Pages 1199-1201

Synthesis of Rotaxanes by Brief Melting of Wheel and Axle Components

Author keywords

Macrocycles; Mechanical binding; Rotaxanes; Supramolecular chemistry; Synthetic methods

Indexed keywords


EID: 0030796997     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199711991     Document Type: Article
Times cited : (63)

References (54)
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    • note
    • We thank Dipl.-Chem. R. Jäger for providing substances and for fruitful discussions.
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    • We know from experience that Stuart/Briegleb models of large molecules are often too flexible, whereas CPK models are usually too rigid.
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    • It is conceivable that at high temperatures the rotaxane construction takes place by a bond cleavage (e.g. CO-NH) and subsequent threading and recombination. The fact that we could not find any catenanes refutes a mechanism of bond cleavages in the wheel, particularly since the number of the amide bonds (although sterically more hindered) is twice the number of those in the axle. Furthermore we could not lind any thermal/pyrolytic cleavage/recombination of amide bonds in the literature apart from transamidations, which proceed by addition and elimination at 200°C: H. R. Kricheldorf, E. Leppert, G. Schilling, Makromol. Chem. 1975, 176, 1629.
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    • note
    • We thank Prof. Dr. P. von R. Schleyer (Universität Erlangen-Nürnberg, Prof. Dr. J. Gasteiger (Computer-Chemie-Centrum Erlangen-Nürnberg), and Dr. B. Schürmann (Humboldt-Universität Berlin) for the cooperation with calculations.
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    • We have also tried to synthesize these rotaxanes by slowly heating corresponding mixtures of wheel and axle in an oil bath (to 320°C). This led to decreased yields of the corresponding rotaxanes and increased portions of by-products.


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